Iron(III)-Catalyzed Carboannulations of Homopropargylic Alcohols: A One-Pot General Synthesis of 4-(2,2-Diarylvinyl)quinolines and 4-(2,2-Diarylvinyl)-2<i>H</i>-chromenes

De, Sukanya; Chowdhury, Chinmay

doi:10.1021/acs.joc.3c00442

Cited by 6 publications

(2 citation statements)

References 64 publications

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“…The synthetic tricyclic chromene with the exocyclic benzylidene moiety also showed strong antileishmanial acitivity . As a result, the development of elegant synthetic methodologies for diverse chromane derivatives is a highly active area in organic synthesis. , Until now, many efforts have been devoted to the access of various polysubstituted chromanes. , However, there are still some shortcomings in the known synthetic methods for multifunctionalized chromene derivatives. , Development of efficient, green, and environment-friendly synthetic protocols for diverse chromene derivatives is very necessary …”

Section: Introductionmentioning

confidence: 99%

Construction of Diverse Fused Chromene Frameworks via Isocyanide-Based Three-Component Reaction

He,

Huang,

Huang

et al. 2024

J. Org. Chem.

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A convenient synthetic protocol for diverse fused chromenes was successfully developed by a three-component reaction of alkyl isocyanides, dialkyl but-2-ynedioates, and various cyclic 1,3-dipolarophiles containing o-hydroxyphenyl group. In the absence of any catalyst, the three-component reaction of alkyl isocyanides, dialkyl but-2-ynedioates, and 3-(o-hydroxyarylidene)indolin-2-ones in tetrahydrofuran at 60 °C resulted in unique functionalized spiro [cyclobuta[c]chromene-1,3′-indolines] in good yields and with high diastereoselectivity. However, the similar three-component reaction with 2-(5-halo-2-hydroxyarylidene)indolin-2-ones afforded unexpected chain products in satisfactory yields. In addition, the three-component reaction of alkyl isocyanides, dialkyl but-2-ynedioates, and 2-(o-hydroxyarylidene)-1,3-indanediones in tetrahydrofuran at 60 °C resulted in complex indeno[2′,1′:5,6]pyrano [3,4-c]chromene derivatives in high yields and with high diastereoselectivity.

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Section: Introductionmentioning

confidence: 99%

Construction of Diverse Fused Chromene Frameworks via Isocyanide-Based Three-Component Reaction

He,

Huang,

Huang

et al. 2024

J. Org. Chem.

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“…Due to the critical scientific appeal and ubiquity of the quinoline core in contemporary agrochemical and pharmaceutical areas, the development of novel approaches for the generation of the pivotal skeletal motif remains a hot spot and is attracting increasing attention . In 2016, the Jiang group developed a concise and general protocol employing o -vinylanilines and alkynes as the substrates, with PdCl 2 as the catalyst, Cu(TFA) 2 as the additive, and molecular oxygen as the terminal oxidant, thereby furnishing synthetically useful 2,3-disubstituted quinolines (Scheme a) .…”

Section: Introductionmentioning

confidence: 99%

Lewis Acid Catalyzed [4 + 2] Annulation of Propargylic Alcohols with 2-Vinylanilines

Ren,

Feng,

Zhang

et al. 2023

J. Org. Chem.

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An elegant Lewis acid catalyzed, protection-free, and straightforward synthetic strategy for the assembly of a series of sophisticated polycyclic quinoline skeletons employing propargylic alcohols and 2-vinylanilines as the substrates in the presence of Yb(OTf) 3 (10 mol %) and AgOTf (10 mol %) in tetrahydrofuran has been described. This annulation protocol, which proceeds through a sequential Meyer−Schuster rearrangement/nucleophilic substitution/deprotonation sequence, provides a versatile, practical, and atom-economical approach for accessing quinoline derivatives in moderate-to-good yields.

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K₃PO₄–Mediated Synthesis of Chromeno–[3,4‐c]isoxazole from 3–Nitro–2H–chromene and α–Chloro Aldehyde via Michael Addition/C−Cl Bond Cleavage/Deformylation as Key Fragmentation Sequences

Pratap,

Shukla,

Giri

et al. 2024

Adv Synth Catal

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Here we report a transition metal– and oxidant–free annulation cascade method for the synthesis of chromeno–isoxazoles. The annulation reaction involves easily accessible starting materials, 3‐nitro‐2H‐chromene and α‐chloro aldehyde, yielding the structurally intriguing framework, chromeno[3,4‐c]isoxazoles employed by tripotassium phosphate as a base. The isoxazole ring construction over the 2H–chromene unit is believed to occur via a series of multiple reaction sequences. Here, the enolate generation/Michael addition/C–Cl bond cleavage/oxy–anionic addition to reactive tethered‐aldehyde/deformylation via retro– C–C and N–O bond cleavages are the most possible sequences which furnish the desired end–product in good chemical yields. The multiple reaction sequences occur in one‐pot at mild conditions, supported by experimental results and a few control experiments including DFT studies. This process exhibits a broad substrates scope illustrating good functional group compatibility towards both the nitrochromenes and aldehydes, and thus prove to be a general and efficient protocol for the synthesis of chromeno[3,4–c]isoxazoles. Overall, the use of nitrochromene as the limiting reagent, noteworthy functional group tolerance, scalability including great applications like chiral pool strategy towards the synthesis of enantioenriched chromeno‐isoxazole are the additional features.

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Iron(III)-Catalyzed Carboannulations of Homopropargylic Alcohols: A One-Pot General Synthesis of 4-(2,2-Diarylvinyl)quinolines and 4-(2,2-Diarylvinyl)-2H-chromenes

Cited by 6 publications

References 64 publications

Construction of Diverse Fused Chromene Frameworks via Isocyanide-Based Three-Component Reaction

Construction of Diverse Fused Chromene Frameworks via Isocyanide-Based Three-Component Reaction

Lewis Acid Catalyzed [4 + 2] Annulation of Propargylic Alcohols with 2-Vinylanilines

K₃PO₄–Mediated Synthesis of Chromeno–[3,4‐c]isoxazole from 3–Nitro–2H–chromene and α–Chloro Aldehyde via Michael Addition/C−Cl Bond Cleavage/Deformylation as Key Fragmentation Sequences

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Iron(III)-Catalyzed Carboannulations of Homopropargylic Alcohols: A One-Pot General Synthesis of 4-(2,2-Diarylvinyl)quinolines and 4-(2,2-Diarylvinyl)-2H-chromenes

Cited by 6 publications

References 64 publications

Construction of Diverse Fused Chromene Frameworks via Isocyanide-Based Three-Component Reaction

Construction of Diverse Fused Chromene Frameworks via Isocyanide-Based Three-Component Reaction

Lewis Acid Catalyzed [4 + 2] Annulation of Propargylic Alcohols with 2-Vinylanilines

K3PO4–Mediated Synthesis of Chromeno–[3,4‐c]isoxazole from 3–Nitro–2H–chromene and α–Chloro Aldehyde via Michael Addition/C−Cl Bond Cleavage/Deformylation as Key Fragmentation Sequences

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K₃PO₄–Mediated Synthesis of Chromeno–[3,4‐c]isoxazole from 3–Nitro–2H–chromene and α–Chloro Aldehyde via Michael Addition/C−Cl Bond Cleavage/Deformylation as Key Fragmentation Sequences